Whirligig opens with Brent Bishop, a high school junior, playing video games. Brent’s mother calls him to dinner. While eating, the family has a clipped conversation about the commercials on TV. Brent and his parents have been eating TV dinners since moving from Atlanta to Chicago, following his father’s promotion at work. Despite their improved financial situation, Brent thinks that his father seems stressed and unhappy.

Brent grooms himself for a party that night, carefully picking out an outfit that will “impress without risking being made fun of” (4).His family has moved four times due to his father’s “corporate climb,” and Brent has tried hard to fit in at each new place, noting the ear in which the boys wear their earrings and finding the “cool” music stations (6). Brent rejoiced when he heard he would be going to a private school in Chicago, but has found that he seems “a lot poorer than before,” surrounded by his new wealthy classmates (8).

Brent picks up his friend Jonathan. When they arrive at the party, he finds that everyone is dressed in black or white to participate in a human chess game, and is furious that Jonathon forgot about the dress code.